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Reductive double electrophilic reactions of methyl thiophenecarboxylate mediated by samarium diiodide and hexamethylphosphoramide

✍ Scribed by Shyh-Ming Yang; Jim-Min Fang

Book ID
104256492
Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
242 KB
Volume
38
Category
Article
ISSN
0040-4039

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✦ Synopsis

The pentadienyl anion generated by treating methyl thiophenecarboxylate with samarium diiodideY hexamethylphosphoramide in tetrahydrofuran reacts at the C-5 position with a series of benzaldehydes and acetophenones to give the intermediates of samarium dienolates, which ale wapped with the second electrophile, such as acetic anhydride, benzyl bromide and em-bonyl compounds, in regioselectiw mAnn~'$ depending on the nature of the eleorophile. Thus, the tl~ee-component reactions of methyl thiophenecarboxylate with carbonyl compounds are achieved in a one-pot procedure to give 4,5-disubstituted-4,5-dihydrothiophenecarboxylates.

πŸ“œ SIMILAR VOLUMES

ChemInform Abstract: Distant Functionali
ChemInform Abstract: Distant Functionalization via Incorporation of Thiophene Moieties in Electrophilic Reactions Promoted by Samarium Diiodide.
✍ Shyh-Ming Yang; Sandip Kumar Nandy; Anandakathir Robinson Selvakumar; Jim-Min Fa πŸ“‚ Article πŸ“… 2001 πŸ› John Wiley and Sons βš– 38 KB

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